If you are picturing sugar-white sand under 72 degree sunshine while friends back home are scraping ice off their cars, you are picturing Clearwater Beach in winter. This is our favorite season on Florida’s Gulf Coast, and at Endless Stays we spend a lot of time here designing homes that make the most of it.
Winter on Clearwater is quieter than spring break, cheaper than summer, and just warm enough to feel like a vacation the moment you step off the plane. The Gulf is calm, the sunsets stretch long, and the dolphins show up like clockwork on the afternoon tours.
In this guide we cover what winter weather is really like, the best beaches and attractions, our go-to seafood spots, the boat tours worth booking, and how to pick a place to stay that fits the season.
What Clearwater Beach in Winter Actually Feels Like
Winter on Clearwater Beach runs from December through February, with cool but comfortable weather and much smaller crowds than you get later in spring.
Here is what to expect:
- Daytime highs: about 70 to 73 degrees Fahrenheit, sunny most days.
- Nighttime lows: in the low to mid 50s, so bring a light jacket for evenings.
- Gulf water temperature: roughly 62 to 66 degrees, coldest in January.
- Rainfall: low, usually 3 to 5 rainy days per month.
- Crowds: quiet in early December and January, busier around Christmas week and mid February.
The beach is absolutely swimmable for anyone from a colder climate who does not mind a brisk dip, and it is perfect for long walks, sunbathing, shelling, and everything on the water. Locals tend to trade full-day beach sessions for morning walks and afternoon sun, then head to a rooftop or a waterfront restaurant when the breeze picks up after sunset.
Quick insight: January is statistically the coldest, quietest, and cheapest month of the winter, which is exactly why so many long-stay snowbirds pick it.
The Best Things to Do at Clearwater Beach in Winter
The great thing about visiting in winter is that almost everything is open, but nothing is packed. These are the spots we send our guests to first.
Pier 60
Pier 60 is the heart of Clearwater Beach, a 1,080 foot fishing pier that also happens to be the best sunset spot in town. In winter the light hits earlier (sunset is around 5:45 pm in December and just after 6 pm in February), which makes it easy to stroll out with a coffee and still be back for dinner.
- Location: at the west end of Causeway Blvd, Clearwater, FL 33767
- Best for: sunset walks, fishing, people watching, and Sunsets at Pier 60 vendors most evenings
- Winter tip: bring a light layer, the breeze on the pier is noticeably cooler than on the sand
Sunsets at Pier 60
Sunsets at Pier 60 is a nightly festival that turns the pier and adjoining park into a little open-air market about two hours before sundown. Local artisans, buskers, jugglers, and food vendors all set up along the boardwalk. Winter is one of the best times to catch it because the temperature is mild and the vendor lineup is at full strength for snowbird season.
- Address: 1 Causeway Blvd, Clearwater, FL 33767
- Hours: 4 to 8 pm daily, weather permitting
- Rating: 4.7 stars with more than 1,800 reviews
- Cost: free to walk around, vendors sell crafts and snacks
Learn more about Sunsets At Pier 60
Clearwater Marine Aquarium
The Clearwater Marine Aquarium is a rescue and rehab center as much as an aquarium, and it is our go-to recommendation for any cool or breezy day. This is where Winter the dolphin lived, and the exhibits focused on sea turtles, otters, and stingrays are genuinely educational without feeling dumbed down. Around the holidays they run Winter’s Wonderland, with lights and seasonal programming that usually stretches into the first week of January.
- Address: 249 Windward Passage, Clearwater, FL 33767
- Phone: (727) 441-1790
- Hours: 10 am to 5 pm daily
- Rating: 4.2 stars from over 20,000 reviews
- Good to know: buy tickets online, weekends and holiday weeks can sell out
Learn more about Clearwater Marine Aquarium
Caladesi Island State Park
If you want to see what this coastline looked like before the resorts arrived, spend a morning on Caladesi. It is a barrier island reachable by a short ferry ride from Honeymoon Island (or a beach hike from the north end of Clearwater Beach if the tide cooperates). Winter is peak time for shelling here, and the water is calm enough for kayaking through the mangrove trail.
- Ferry from: 1 Causeway Blvd, Dunedin, FL 34698
- Phone: (727) 469-5918
- Rating: 4.8 stars from 3,000+ reviews
- Winter tip: ferries have limited winter schedules, check the day before
Learn more about Caladesi Island State Park
Sand Key Park
Just across the bridge south of Clearwater Beach, Sand Key Park is where locals go when they want a quieter beach day. Wide sand, natural dunes, picnic pavilions, and much easier parking than the main beach. In winter you can walk for a mile without dodging anyone, and the sunset views rival Pier 60 without the crowd.
- Address: 1060 Gulf Blvd, Clearwater, FL 33767
- Phone: (727) 582-2100
- Rating: 4.7 stars from over 10,000 reviews
- Best for: quiet beach days, families, dog park lovers (there is a fenced beach for dogs)
Learn more about Sand Key Park
Winter Boat Tours: Dolphins, Pirates, and Sunset Sails
The Gulf is at its calmest in winter, which makes this one of the best times of the year to get on a boat. Sightings of bottlenose dolphins are common and the water is clear enough to see them wake-surfing behind the boat.
Little Toot Dolphin Adventure
Little Toot is the boat we recommend if you only have time for one tour. It runs multiple times a day out of Clearwater Marina, and the crew genuinely knows where the resident dolphin pods hang out. Tours run about 90 minutes and cover a good stretch of the intracoastal.
- Address: 25 Causeway Blvd #12, Clearwater Beach, FL 33767
- Phone: (727) 446-5503
- Rating: 4.9 stars from nearly 2,700 reviews
- Winter tip: book the 2 pm or sunset departure, mornings on the water can feel chilly
Learn more about Little Toot Dolphin Adventure
Captain Memo’s Pirate Cruise
If you are traveling with kids or grandkids in the December or February holiday windows, Captain Memo’s is worth every dollar. It is a full pirate ship experience with face painting, water gun battles, and a sunset cruise option that adults quietly love as much as the kids do.
- Address: 25 Causeway Blvd, Clearwater Beach, FL 33767
- Phone: (727) 446-2587
- Rating: 4.7 stars from over 1,500 reviews
- Best for: families, birthdays, and adults who order the cruise-and-cocktails sunset option
Learn more about Captain Memo’s Pirate Cruise
Did you know? Winter is the least crowded season on the water. Sunset cruises that sell out in June still have same-day availability most weeknights in January.
Where to Eat: Our Favorite Waterfront Restaurants
Clearwater’s food scene is casual and heavy on seafood, which is exactly what you want after a beach day. These two are on our short list.
Frenchy’s Original Cafe
Frenchy’s is a Clearwater institution and the grouper sandwich is the reason you go. This is the original location, a block off the beach on Baymont, and it has the kind of dim wood-paneled dive feel that you only get from a place that has been busy since 1981. In winter you can usually walk right in at lunch, which is almost impossible in April.
- Address: 41 Baymont St, Clearwater, FL 33767
- Phone: (727) 446-3607
- Hours: 11 am to 9 pm daily
- Rating: 4.5 stars from over 3,000 reviews
- What to order: the original grouper sandwich, she-crab soup, and a bucket of Yuenglings
Learn more about Frenchy’s Original Cafe
Bait House Tackle & Tavern
The Bait House sits right on Clearwater Marina next to the dolphin boat docks, which makes it the best spot in town for a post-cruise lunch. Big open-air deck, watch the pelicans dive, order a smoked fish spread and a rum drink. The vibe is easy and the sunset view from the deck is one of the best in Clearwater without needing a reservation.
- Address: 45 Causeway Blvd, Clearwater, FL 33767
- Phone: (727) 446-8134
- Hours: 11:30 am to 10 pm daily
- Rating: 4.7 stars from over 3,100 reviews
- Best for: post-boat-tour lunches, sunset drinks, casual dinner with a view
Learn more about Bait House Tackle & Tavern
Rainy Day and Cool Day Backups
We do not get a lot of grey days in a Clearwater winter, but when the wind picks up or a front rolls through, it helps to have a Plan B. These are ours.
Captain Bligh’s Landing
Captain Bligh’s Landing is a two-course pirate-themed mini golf spot right on South Gulfview, three minutes from the sand. It stays open late (10 pm most nights), and on a breezy 60 degree evening it turns into the easiest way to keep the group happy after the beach shuts down. Bring quarters for the arcade attached.
- Address: 630 S Gulfview Blvd, Clearwater, FL 33767
- Phone: (727) 443-6348
- Hours: 10 am to 10 pm daily
- Rating: 4.3 stars from over 900 reviews
Learn more about Captain Bligh’s Landing
Weeki Wachee Springs State Park (Day Trip)
If you are willing to drive about 75 minutes north, Weeki Wachee is the kind of place we tell every winter visitor about at least once. It is a natural spring that stays a constant 74 degrees year-round, which means it is warmer than the Gulf all winter long. Kayaking here in January is genuinely magical, and the classic mermaid shows are a piece of old-Florida history worth seeing at least once.
- Address: 6131 Commercial Way, Spring Hill, FL 34606
- Phone: (352) 610-5660
- Hours: 9 am to 5:30 pm daily
- Rating: 4.5 stars from over 9,300 reviews
- Winter bonus: cold Gulf water sends manatees into nearby warm springs, this is one of the best times of year to spot them
Learn more about Weeki Wachee Springs State Park
Winter Events Worth Planning Around
If you want to time your visit around something specific, these are the Clearwater winter events that consistently deliver.
- Beach Christmas Tree Lighting at Pier 60 (early December): free, family-friendly, palm-tree-topped Christmas tree lit at sunset with live music.
- Clearwater Yacht Club Holiday Boat Parade (mid December): dozens of decorated boats cruise the harbor, best viewed from a waterfront restaurant or a dock.
- Winter’s Wonderland at the Clearwater Marine Aquarium (mid November through early January): holiday décor, lights, and special programming layered onto the regular aquarium visit.
- Sunset to Sparkle at Pier 60 (New Year’s Eve): fireworks, live music, and the Pier 60 vendors extended into a full beach party.
- Clearwater Sea-Blues Festival (February): outdoor festival mixing local seafood with a lineup of blues, jazz, and roots artists.
- Phillies Spring Training (starts late February at BayCare Ballpark): the reason a lot of long-stay guests time their trip to late February through March.
Local tip: if you want a room for the boat parade or New Year’s Eve, we start recommending guests book by late September. Everything else in winter tends to have real availability inside of two weeks.
Where to Stay for a Clearwater Beach Winter Trip
The right base for a winter trip depends on how you like to travel. In our experience, families and groups have a much better time in a private home with room to spread out than in a single hotel room, especially over Christmas week or when the group has three or four generations under one roof.
That is what we do at Endless Stays. Our Clearwater, FL vacation rentals are professionally designed with pools, hot tubs, and the kind of themed spaces (theater rooms, arcades, game rooms) that turn a rainy day into a highlight. In winter, a heated private pool is genuinely a game changer because the Gulf is on the cool side.
A few things we recommend guests look for when booking a Clearwater Beach winter stay:
- Heated pool. The air is warm, the Gulf is chilly, a heated pool bridges the gap.
- Space to gather. Winter trips skew multi-generational, look for open kitchens and a living space that seats everyone.
- Walk score to the beach or Pier 60. The best Clearwater winter routine is beach in the morning, walk to Pier 60 at sunset.
- Flexibility on stay length. January and February are the sweet spot for monthly rentals, and many of our snowbird guests stretch to 30 days for the better rate.
If you want help matching a property to your dates, our concierge team can hand-pick a shortlist. Browse the collections if you would rather start from a specific vibe (heated pools, game rooms, family layouts).
Best Time to Visit Clearwater Beach in Winter
Every winter month has a personality. Here is how to think about it.
- Early December: quietest week of the season, lowest prices, mild sunny days. Best if you want a peaceful beach reset.
- Christmas and New Year’s week: the beach turns festive, the boat parade lights up the harbor, and prices spike. Book early.
- January: the coldest month for water, the warmest month for deals. Sunny, mild, and blissfully quiet after New Year’s.
- February: slightly warmer, more festivals, snowbird season in full swing. Late February brings Phillies spring training and the season starts to pick back up.
What to Pack for Clearwater Beach in Winter
Winter packing here is not what most first-time visitors expect. Here is our short list.
- Layers. Daytime is t-shirt weather, evenings need a light jacket or fleece.
- Swimsuit and rashguard. For a quick dip in the Gulf, or a longer session in a heated pool.
- Real walking shoes. You will end up on Pier 60, Sand Key, and probably a state park.
- Sunscreen. The winter sun is deceptive, you will still burn.
- Small binoculars. Great for dolphin cruises and manatee spotting.
- A reusable water bottle. Especially if you plan on a day trip to the springs.
Plan Your Clearwater Beach Winter Escape
Clearwater Beach in winter is one of those trips people take once and then repeat every year. The weather is mild, the crowds are thin, and every classic Clearwater experience (Pier 60, the dolphin tours, Frenchy’s grouper sandwich) is easier to enjoy without the summer chaos.
At Endless Stays, we build our homes around the seasons our guests actually want to travel. If you are thinking about a winter trip, we would love to help you find the right place to stay. Browse our Clearwater Beach vacation rentals or reach out to our concierge team and we will send you a shortlist that fits your dates, your group, and your winter wish list.
Frequently Asked Questions
Is Clearwater Beach warm enough to visit in winter?
Yes. Daytime highs sit around 70 to 73 degrees Fahrenheit through December, January, and February, which is comfortable for the beach and outdoor activities. Evenings cool into the mid 50s, so pack a light jacket for after sunset.
Can you swim in Clearwater Beach in winter?
You can, but the Gulf runs cool. Water temperatures are usually 62 to 66 degrees, coldest in January. Most visitors take short dips on sunny afternoons rather than long swims. A heated pool at your vacation rental makes a big difference.
When is the least crowded time to visit Clearwater Beach?
Early to mid January, right after New Year’s, is the quietest and cheapest week of the year. Restaurants have open tables, hotels drop rates, and the beach feels wide open. Weekends around Christmas and mid February are the busiest winter windows.
What is there to do at Clearwater Beach in December?
Pier 60 sunsets, the Beach Christmas Tree Lighting, the Yacht Club Holiday Boat Parade, and Winter’s Wonderland at Clearwater Marine Aquarium are the seasonal highlights. Regular boat tours, beach walks, and restaurants like Frenchy’s are all going strong.
Is Clearwater Beach or St. Pete Beach better in winter?
Both are excellent in winter. Clearwater Beach has the wider white-sand beach, Pier 60, and more family attractions like Captain Memo’s and the aquarium. St. Pete Beach has a slightly quieter feel and easier access to downtown St. Pete museums. If it is your first trip to the area, Clearwater is the more classic choice.
How much does a winter trip to Clearwater Beach cost?
January is the cheapest month of the year on the beach, with vacation rental rates often 30 to 50 percent lower than spring break. December and February sit in the middle. Christmas week, New Year’s, and Presidents’ Day weekend are the pricey exceptions.